Nucleophilic alkenes. V. Formation of a naphthalenic system by addition of 1,1-Dimethoxyethene to 2-Acetyl-1,4-benzoquinone and subsequent transformation

Abstract

2-Acetyl-1,4-benzoquinone underwent rapid 1 : 1-addition of 1,1- dimethoxyethene at position 3 to give a 2,3-dihydro-2,2- dimethoxybenzofuran derivative (2). Ring opening of this cyclic orthoester and subsequent ring closure onto the acetyl group gave a naphthalene derivative incorporating the 1,3-dioxygenation pattern found in many polyketides.